A video from inside the castle shows a large hole in the ceiling and a room filled with stone rubble, purportedly from the bombing.

Government troops have been pressing an offensive against rebels in the province in recent months, and the town, which goes by the same name as the castle, has been under attack by regime troops for the past four days.

The Britain-based Syrian Observatory for Human Rights said Syrian warplanes carried out at least three airstrikes in the area on Friday, but the activist group could not confirm whether the fortress itself had been hit. It also said government forces have ordered residents to evacuate the town, apparently in preparation for a full-scale attack on the area.

The imposing Krak des Chevaliers, which towers above the surrounding countryside from its hilltop perch, has a storied history. It held off a siege by the Muslim warrior Saladin nearly 900 years ago, and was lauded centuries later by Lawrence of Arabia for its beauty.

The fortress has already been damaged over the course of the civil war, but if the hit it took Friday is confirmed, it would mark the worst destruction to the building so far.

An amateur video posted to YouTube appeared to show a missile striking one of the castle’s towers, sending a plume of smoke and dust into the sky. The off-camera narrator says the date is July 12, 2013.

The videos appeared genuine and corresponded to other AP reporting on the events depicted.

Many of Syria’s archaeological sites have been badly damaged by the country’s civil war. Aleppo’s centuries-old covered market was gutted by fire last year, while in April, the 11th-century minaret of the famed Umayyad Mosque that towered over the narrow stone alleyways of Aleppo’s old quarter collapsed during fighting between troops and rebels.

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